3.3.14: Organic Synthesis

• Why should chemists aim to design processes that do not require a solvent?

  • Solvents can be expensive
  • Are difficult to dispose of
  • Often cannot be reused after a reaction has taken place
• Why should chemists design processes that use non-hazardous starting materials?

  • Reactions are safer to operate
  • Avoids having to dispose of any unreacted starting materials
• Why should chemists aim to design processes with fewer steps?

  • usually faster & more efficient ∵ less likely to lose more product
• Why should chemists aim to design processes with high atom economy?

  • To avoid waste products
• alkane -> haloalkane

  • reagent: halogen
  • condiitons: UV light
• haloalkane -> alcohol

  • reagents: aqueous NaOH
  • Conditions: warm, reflux
• haloalkane -> alkene

  • reagents: ethanolic KOH
  • conditions: heat, distillation
• haloalkane -> nitrile

  • reagents: aqueous KCN
  • conditions: heat, reflux
• haloalkane -> primary amine

  • reagents: EXCESS NH3
  • conditions: heat
• primary amine -> secondary amine

  • reagents: haloalkane
  • conditions: warm
• secondary amine -> tertiary amine

  • reagents: haloalkane
  • conditions: warm
• tertiary amine -> quaternary ammonium salt

  • reagents: haloalkane
  • conditions: warm
• alkene -> dibromoalkane

  • reagents: Br2
  • conditions: room temperature
• alkene -> bromoalkane

  • reagents: HBr
  • conditions: room temperature
• alkene -> alkylhydrogensulfate

  • reagents: CONCENTRATED H2SO4
  • conditions: cold
• alkylhydrogensulfate -> alcohol

  • reagents: H2O
  • conditions: warm
• alkene -> alcohol

  • reagents: steam
  • conditions: 300 degrees C, 600 kPa, H3PO4 catalyst
• nitrile -> primary amine

  • reagents: LiAlH4
  • conditions: dry ether
• alcohol -> alkene

  • reagents: CONCENTRATED H2SO4
  • conditions: heat, reflux
• primary or secondary alcohol -> carbonyl

  • reagents: acidified K2Cr2O7 / K2Cr2O7 & dilute H2SO4
  • conditions: warm, distillation
• primary alcohol -> carboxylic acid

  • reagents: acidified K2Cr2O7 / K2Cr2O7 & dilute H2SO4
  • conditions: heat, reflux
• aldehyde -> carboxylic acid

  • reagents: acidified K2Cr2O7 / K2Cr2O7 & dilute H2SO4
  • conditions: heat, reflux
• carbonyl -> alcohol

  • reagents: aqueous NaBH4
  • conditions: room temperature
• carboxylic acid -> carboxylate salt

  • reagents: NaOH
  • conditions: room temperature
• amine -> alkylammonium salt

  • reagents: aqueous HCl
  • conditions: room temperature
• carbonyl -> hydroxynitrile

  • reagents: HCN / acidified KCN
  • conditions: room temperature
• acyl chloride -> carboxylic acid

  • reagents: H2O
  • conditions: room temperature
• acyl chloride -> amide

  • reagents: NH3
  • conditions: room temperature
• acid anhydride -> carboxylic acid

  • reagents: H2O
  • conditions: warm
• acid anhydride -> amide

  • reagents: NH3
  • conditions: warm
• carboxylic acid + alcohol -> ester + water

  • reagents: CONCENTRATED H2SO4
  • conditions: heat, reflux
• acyl chloride + alcohol -> ester + hydrogen chloride

  • conditions: room temperature
• acid anhydride + alcohol -> ester

  • conditions: warm
• ester -> carboxylic acid + alcohol

  • reagents: CONCENTRATED H2SO4
• ester -> carboxylate salt + alcohol

  • reagents: aqueous NaOH
  • conditions: heat under reflux
• acyl chloride + primary amine -> N-substituted amide

  • conditions: room temperature
• acid anhydride + primary amine -> N-substituted amine

  • conditions: warm
• benzene -> nitrobenzene

  • reagents: concentrated H2SO4 & HNO3
  • conditions: warm, reflux
• benzene -> phenylalkanone

  • reagents: acyl chloride, AlCl3
  • conditions: room temperature